Cubs fans will be in disbelief after digging deeper into Theo Epstein's executive tree

By the end of the Theo Epstein regime for the Chicago Cubs, there was a clear succession plan in place. Epstein was going to walk at the end of his contract, handing things over to his understudy, Jed Hoyer. The plan was moved up by a year, considering Epstein parted with the Cubs after the 2020 season, considering it was clear that a reset was needed.

Hoyer became the front man for the Cubs' baseball operations, and his original group included one of the final front office hires Epstein made in Craig Breslow. By the time that Epstein left the Cubs, Breslow was rising voice of influence in the Cubs' organization. He was credited with revamping the team's pitching infrastructure, and used that to land the top job with the Boston Red Sox.

Epstein, throughout his career with the Cubs and Boston Red Sox, has widely been viewed as one of the best minds to ever lead a front office, but as the 2026 season is unfolding, his executive tree proves that his guys are in over their head.

Cubs are learning there's only one Theo Epstein

Hoyer and Breslow are the obviouis examples.

As the Cubs' 2026 season goes further and further off the rails, it's becoming clear that there;s a Jed Hoyer problem. Despite the 2025 season being the first year that Hoyer's Cubs reached the postseason, it's looking like the success will be short-lived. Beyond the injuries the Cubs have had this season, the organization appears to be broken. It's hard to imagine that Hoyer will be allowed to oversee another reset, considering that was the original premise of him replacing Epstein and it produced limited success.

In Boston, Breslow appears to be on borrowed time. In fact, Epstein, who is now part of the ownership group of the Red Sox, may not be a fan of how Breslow has ran the front office in recent years. Short of the Red Sox turning their season around, Breslow may be the fall guy come October.

It doesn't stop with Hoyer and Breslow. Like the Cubs and Red Sox, the Detroit Tigers have been one of the biggest disappointments of the 2026 season. While the Tigers have been faced with injuries to Tarik Skubal and Justin Verlander, their offense was dormant during the first two months of the season, begging the question why Scott Harris didn't prioritize the addition of a bat during the offseason. Harris carved his front office chops under Epstein with the Cubs, and there's skepticism in Detroit that he's the right man to lead the path foward.

There's no questioning the executive that Epstein is. But there's more than enough information to suggest his executive tree has been a massive disappointment.

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